EP0451468A1 - Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zu ihrer Herstellung - Google Patents

Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zu ihrer Herstellung Download PDF

Info

Publication number
EP0451468A1
EP0451468A1 EP91102465A EP91102465A EP0451468A1 EP 0451468 A1 EP0451468 A1 EP 0451468A1 EP 91102465 A EP91102465 A EP 91102465A EP 91102465 A EP91102465 A EP 91102465A EP 0451468 A1 EP0451468 A1 EP 0451468A1
Authority
EP
European Patent Office
Prior art keywords
group
alkyl group
haloalkyl
alkyl
hydrogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP91102465A
Other languages
English (en)
French (fr)
Other versions
EP0451468B2 (de
EP0451468B1 (de
Inventor
Fumio Ishihara Sangyo Kaisha Ltd. Kimura
Takahiro Ishihara Sangyo Kaisha Ltd. Haga
Nobuyuki Ishihara Sangyo Kaisha Ltd. Sakashita
Shigeo Ishihara Sangyo Kaisha Ltd. Murai
Yuji Ishihara Sangyo Kaisha Ltd. Nakamura
Shooichi Ishihara Sangyo Kaisha Ltd. Honzawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=12542676&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0451468(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Publication of EP0451468A1 publication Critical patent/EP0451468A1/de
Application granted granted Critical
Publication of EP0451468B1 publication Critical patent/EP0451468B1/de
Publication of EP0451468B2 publication Critical patent/EP0451468B2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to novel substituted pyridinesulfonamide compounds and salts thereof, herbicidal compositions containing them as active ingredients, and a process for their production.
  • 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide (trademark: Glean®) is known as a herbicide which is safe to barley and wheat; ethyl 2-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonylaminosulfonyl]benzoate (trademark: Classic®) is known as a herbicide which is safe to soybean; methyl 2-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonylaminosulfonylmethyl]benzoate (trademark: Londax®) is known as a herbicide which is safe to paddy field rice; and methyl 2-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl-aminosulf
  • the present inventors have conducted syntheses and researches to find sulfonamide compounds which are safe particularly to corn among crop plants, and have finally accomplished the present invention.
  • the present invention provides a novel substituted pyridinesulfonamide compound having the following formula (I): wherein R1 is an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group, R2 is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group, R3 is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylamino group or a dialkylamino group, and each of X and Y which are independent from each other, is a halogen atom, an alkyl group, an alkoxy group or a haloalkoxy group, and its salt.
  • R1 is an alkyl group, a haloalkyl group, an alkoxyalky
  • the present invention also provides a herbicidal composition
  • a herbicidal composition comprising a herbicidally effective amount of the substituted pyridinesulfonamide compound of the formula (I) or its salt, and an agricultural adjuvant.
  • the present invention further provides a method for killing weeds, which comprises applying a herbicidally effective amount of the substituted pyridinesulfonamide compound of the formula (I) or its salt to the locus to be protected.
  • the present invention provides a process for producing a substituted pyridinesulfonamide compound having the formula (I) and its salt, which comprises reacting a substituted pyridine compound having the formula (II): wherein R1, R2 and R3 are as defined above, and Z1 is a -NH2 group, a -NCO group or a -NHCO2R4 group, wherein R4 is an alkyl group or an aryl group, with a pyrimidine compound having the formula (III): wherein X and Y are as defined above, and Z2 is a -NH2 group when Z1 is a -NCO group or a -NHCO2R4 group, and a -NCO group or a -NHCO2R4 group, when Z1 is a -NH2 group, wherein R4 is as defined above.
  • the present invention provides a substituted pyridine intermediate compound having the formula (II-1): wherein R1 is an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group, R2 is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group, and R3 is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylamino group or a dialkylamino group.
  • R1 is an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group
  • R2 is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group
  • pyridinesulfonamide compounds represented by the formula (I'): wherein R1' is an alkyl group or a haloalkyl group, R2' is an alkyl group, R3' is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group or an alkoxyalkyl group, each of X' and Y' which are independent from each other, is a methyl group or a methoxy group, or their salts.
  • R1' is an alkyl group or a haloalkyl group, particularly an alkyl group
  • R2' is an alkyl group
  • R3' is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, or an alkoxyalkyl group
  • each of X' and Y' is a methyl group or a methoxy group
  • R1' and R2' is a methyl group
  • R3' is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group
  • each of X' and Y' which are independent from each other, is a methoxy group.
  • the alkyl group or the alkyl moiety in the definition of R1, R2, R3, X and Y in the above formula (I) is preferably a C1-C4 alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group;
  • the alkenyl group in the definition of R1 and R2 is preferably a C2-C4 alkenyl group such as a propenyl group or a butenyl group;
  • the halogen atom in the definition of R1, R2, R3, X and Y may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the salt of the compound of the present invention may, for example, be an alkali metal salt such as a sodium salt or a potassium salt, an alkaline earth metal salt such as a magnesium salt or a calcium salt, or a quaternary ammonium salt such as a methylamine salt, a dimethylamine salt or a triethylamine salt.
  • an alkali metal salt such as a sodium salt or a potassium salt
  • an alkaline earth metal salt such as a magnesium salt or a calcium salt
  • a quaternary ammonium salt such as a methylamine salt, a dimethylamine salt or a triethylamine salt.
  • novel substituted pyridinesulfonamide compound of the above formula (I) can be prepared by e.g. the following methods (A) to (D):
  • R1 is an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group
  • R2 is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group or an alkenyl group
  • R3 is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkylamino group or a dialkylamino group
  • each of X and Y which are independent from each other, is a methyl group or a methoxy group
  • R4 is an alkyl group or an aryl group.
  • the alkyl group for R4 may be the same alkyl group as mentioned with respect to R1, R2 and R3, and the aryl group for R4 may be a phenyl group, a phenyl group substituted by a chlorine atom, a phenyl group substituted by a methyl group, or a naphthyl group.
  • the reaction (A) is conducted in the presence of a base, and the reactions (B), (C) and (D) may also be conducted in the presence of a base as the case requires.
  • a base a tertiary amine such as triethylamine, or 1,8-diazabicyclo[5.4.0]-7-undecene may be used.
  • the reactions (A), (B), (C) and (D) may be conducted in the presence of a solvent as the case requires.
  • the solvent may be an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene; a cyclic or non-cyclic aliphatic hydrocarbon such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, hexane or cyclohexane; an ether such as diethyl ether, dioxane or tetrahydrofuran; a nitrile such as acetonitrile, propionitrile or acrylonitrile; an ester such as methyl acetate or ethyl acetate; or an aprotic polar solvent such as dimethylsulfoxide or sulforane.
  • aromatic hydrocarbon such as benzene, toluene, xylene or chloro
  • the reaction (A) is conducted usually at a reaction temperature of from -20 to +100°C, preferably from 0 to 40°C for a reaction time of from 0.01 to 24 hours, preferably from 0.1 to 1.5 hours; the reaction (B) is conducted usually at a reaction temperature of from 0 to 150°C for a reaction time of from 0.1 to 24 hours; the reaction (C) is conducted usually at a reaction temperature of from 0 to 150°C for a reaction time of from 0.1 to 24 hours; and the reaction (D) is conducted usually at a reaction temperature of -20 to +150°C, preferably from 50 to 110°C for a reaction time of from 0.1 to 24 hours.
  • the compound of the formula (II-1) used as the starting material for the reactions (A) and (B) can be prepared by e.g. the following methods (E), (F) and (G):
  • R1, R2 and R3 are as defined above, T is a chlorine atom or a bromine atom, and Hal is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • Ph represents a phenyl group
  • Bu(t) represents a tert-butyl group
  • aq. represents an aqueous solution.
  • R1, R2, R5, T, Bu(t) and aq. are as defined above.
  • the compounds of the formula (II-2) in the reaction (C) can be prepared by e.g. the following method (J), and the compounds of the formula (II-3) in the reaction (D) can be prepared by e.g. the following method (K).
  • R4 is as defined above.
  • the substituted pyridinesulfonamide compound of the formula (I) can be also produced by another method as follows.
  • the raw material of the formula (II-5) in the reaction formula (L) can be produced, for example, by the method (M).
  • R1, R2, R3, X, Y and Bu(t) in the reaction formula are as defined above.
  • reaction conditions for the respective reactions (E) to (M) such as the reaction temperatures, the reaction times and the solvents and alkaline substances to be used as the case requires, may suitably be selected from the reaction conditions commonly employed in similar reactions, unless otherwise specified.
  • the salts of the substituted pyridinesulfonamide compounds of the present invention can readily be prepared by usual methods.
  • the intermediate compounds of the formula (II-1) are novel compounds, and their typical examples will be given in Table 1.
  • R1' is an alkyl group or a haloalkyl group
  • R2' is an alkyl group
  • R3' is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group or an alkoxyalkyl group.
  • R1' is an alkyl group
  • R2' is a methyl group
  • R3' is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group.
  • the substituted pyridinesulfonamide compounds of the present invention exhibit safety to corn and at the same time exhibit a wide herbicidal spectrum including gramineous weeds at a low dose.
  • herbicidal compositions of the present invention may be applied to various places including agricultural fields such as upland fields, orchards, mulberry fields and non-agricultural fields such as forests, farm roads, open grounds and factory sites.
  • the manner of application may suitably be selected from the soil treatments and foliage treatments.
  • the active ingredients are usually mixed with various agricultural adjuvants such as a carrier, a diluent, a solvent, an emulsifier, a spreader and a surfactant, as the case requires, and may be formulated in various formulations such as granules, water dispersible granules, wettable powders, emulsifiable concentrates, water-soluble powders or soluble concentrates.
  • the weight ratio of the active ingredient to the agricultural adjuvants is usually from 1:99 to 90:10, preferably from 5:95 to 80:20.
  • the suitable dose of the active ingredient can not simply be determined since it may vary depending upon the weather condition, the soil condition, the type of the formulation, the types of the weeds to be controlled, the season for the application, etc. However, it is usual that the effective dose is within a range of from 0.005 to 50 g/a, preferably from 0.01 to 10 g/a, more preferably from 0.05 to 5 g/a.
  • the herbicidal compositions of the present invention may be used in combination with or together with other agricultural chemicals, agricultural adjuvants or phytotoxicity-reducing agents. In such a combination, they may exhibit even better effects or activities.
  • the following compounds may be mentioned, for example, as the active ingredients of such other herbicides. In some cases, synergistic effects may be obtained.
  • an agricultural spreader was further added in an amount to bring the concentration to 0.2%, followed by foliage treatment by means of a small size spray. Seventeen to thirtyfive days after the treatment, the growth of the respective plants were visually inspected, and the degree of growth inhibition was evaluated on a scale of 10 grades in which 10 indicates that the plant was completely killed and 1 indicates no effects, as shown in Table 3 below.
  • a mixture of components (1) to (4) is mixed with compound No. 4 in a weight ratio of 9:1 to obtain a wettable powder.
  • the above components are mixed to obtain a wettable powder.
  • the above components are mixed to obtain a wettable powder.
  • the above components (1) to (4) are uniformly mixed and pulverized by a Dyno mill (manufactured by Willey et Barhofen Co.) to obtain a suspension composition.
  • the above compounds (1) to (5) are introduced into a mixing and refining machine with high speedy and 20% of water is added thereto. They are uniformly mixed, granulated and dried to obtain a water dispersible granules.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP91102465A 1990-02-20 1991-02-20 Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zu ihrer Herstellung Expired - Lifetime EP0451468B2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP3906390 1990-02-20
JP3906390 1990-02-20
JP39063/90 1990-02-20

Publications (3)

Publication Number Publication Date
EP0451468A1 true EP0451468A1 (de) 1991-10-16
EP0451468B1 EP0451468B1 (de) 1996-05-01
EP0451468B2 EP0451468B2 (de) 2000-03-08

Family

ID=12542676

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91102465A Expired - Lifetime EP0451468B2 (de) 1990-02-20 1991-02-20 Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zu ihrer Herstellung

Country Status (8)

Country Link
US (1) US5139565A (de)
EP (1) EP0451468B2 (de)
JP (1) JPH04234850A (de)
AT (1) ATE137500T1 (de)
DE (1) DE69119135T2 (de)
DK (1) DK0451468T3 (de)
ES (1) ES2089041T5 (de)
GR (2) GR3020583T3 (de)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0496608A1 (de) * 1991-01-24 1992-07-29 ISHIHARA SANGYO KAISHA, Ltd. Substituierte Pyridinsulfonamide oder deren Salze, Verfahren zur Herstellung und diese enthaltende Herbizide
EP0508348A1 (de) * 1991-04-11 1992-10-14 Hoechst Schering AgrEvo GmbH Verfahren zur Herstellung von 2-Pyridylsulfonylharnstoffen und Thiadiazolopyridine als Zwischenprodukte in diesem Verfahren
EP0521500A1 (de) * 1991-07-05 1993-01-07 Hoechst Schering AgrEvo GmbH Salze von Pyridylsulfonylharnstoffen als Herbizide und Pflanzenwachstumsregulatoren, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0555770A1 (de) * 1992-02-14 1993-08-18 Hoechst Schering AgrEvo GmbH N-Heteroaryl-N'-(pyrid-2-yl-sulfonyl)-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP0562731A1 (de) * 1992-03-10 1993-09-29 ISHIHARA SANGYO KAISHA, Ltd. Substituierte Pyridinsulfonamidverbindungen und ihre Salze, Verfahren zu ihrer Herstellung und diese enthaltende Herbizide
US5348933A (en) * 1991-01-24 1994-09-20 Ishihara Sangyo Kaisha, Ltd. Substituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same
FR2703685A1 (fr) * 1993-04-09 1994-10-14 Hoechst Schering Agrevo Gmbh Pyridylsulfonylurées à substitution fluorométhylsulfonyle, utilisées comme herbicides, procédé pour les prépararer, et leur utilisation.
US5494886A (en) * 1990-01-10 1996-02-27 Hoechst Aktiengesellschaft Pyridyl sulphonyl ureas as herbicides and plant growth regulators
US5635451A (en) * 1990-01-10 1997-06-03 Hoechst Schering Agrevo Gmbh Pyridylsulfonylureas as herbicides and plant growth regulators, processes for their preparation and their use
US5663118A (en) * 1992-06-08 1997-09-02 Hoechst Schering Agrevo Gmbh Fluoromethylsulfonyl-substituted pyridylsulfonylureas as herbicides, process for their preparation, and their use
US5847146A (en) * 1992-02-14 1998-12-08 Hoechst Schering Agrevo Gmbh N-heteroartyl-n'-(pyrid-2yl-sulfonyl) ureas, processes for their preparation, and their use as herbicides and plant growth regulators

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5209770A (en) * 1989-05-26 1993-05-11 E. I. Du Pont De Nemours And Company Herbicidal pyridinesulfonylureas

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4632695A (en) * 1983-02-04 1986-12-30 Ciba-Geigy Corporation N-phenylsulfonyl-N'-triazinylureas as herbicides and plant growth regulants
US4657578A (en) * 1984-11-15 1987-04-14 E. I. Du Pont De Nemours And Company Herbicidal ortho-heterocyclic sulfonamides
US4668279A (en) * 1984-08-08 1987-05-26 E. I. Du Pont De Nemours And Company Herbicidal pyridinesulfonamides
EP0232067A2 (de) * 1986-01-30 1987-08-12 Ishihara Sangyo Kaisha Ltd. Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zur Herstellung dieser Verbindungen

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4522645A (en) * 1978-12-04 1985-06-11 E. I. Du Pont De Nemours And Company Agricultural pyridinesulfonamides
US4544401A (en) * 1979-10-22 1985-10-01 E. I. Du Pont De Nemours And Company Agricultural pyridinesulfonamides
US4435206A (en) * 1978-12-04 1984-03-06 E. I. Du Pont De Nemours And Company Agricultural pyridinesulfonamides
US4456469A (en) * 1980-03-07 1984-06-26 E. I. Du Pont De Nemours And Company Pyridyl sulfone herbicides
US4605432A (en) * 1980-03-07 1986-08-12 E. I. Du Pont De Nemours And Company Pyridyl sulfone herbicides
US4789393A (en) * 1986-03-07 1988-12-06 E. I. Du Pont De Nemours And Company Herbicidal pyridine sulfonamides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4632695A (en) * 1983-02-04 1986-12-30 Ciba-Geigy Corporation N-phenylsulfonyl-N'-triazinylureas as herbicides and plant growth regulants
US4668279A (en) * 1984-08-08 1987-05-26 E. I. Du Pont De Nemours And Company Herbicidal pyridinesulfonamides
US4657578A (en) * 1984-11-15 1987-04-14 E. I. Du Pont De Nemours And Company Herbicidal ortho-heterocyclic sulfonamides
EP0232067A2 (de) * 1986-01-30 1987-08-12 Ishihara Sangyo Kaisha Ltd. Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zur Herstellung dieser Verbindungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 102, No. 7, February 18, 1985, Columbus, Ohio, USA; LEJEUNE, R. et al.: "Preparation of the disulfide of 3-mercaptopyridine-2- sulfonamide", page 582, column 1, abstract -No. 62 050z *

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5494886A (en) * 1990-01-10 1996-02-27 Hoechst Aktiengesellschaft Pyridyl sulphonyl ureas as herbicides and plant growth regulators
US5635451A (en) * 1990-01-10 1997-06-03 Hoechst Schering Agrevo Gmbh Pyridylsulfonylureas as herbicides and plant growth regulators, processes for their preparation and their use
US5576440A (en) * 1990-01-10 1996-11-19 Hoechst Aktiengesellschaft 2-pyridylsulfonamides
US5529976A (en) * 1990-01-10 1996-06-25 Hoechst Aktiengesellschaft Pyridyl sulphonyl ureas as herbicides and plant growth regulators
US5457084A (en) * 1991-01-24 1995-10-10 Ishihara Sangyo Kaisha Ltd. Substituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same
US5348933A (en) * 1991-01-24 1994-09-20 Ishihara Sangyo Kaisha, Ltd. Substituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same
CN1038012C (zh) * 1991-01-24 1998-04-15 石原产业株式会社 含有取代的吡啶磺酰胺化合物或其盐的除草剂
EP0496608A1 (de) * 1991-01-24 1992-07-29 ISHIHARA SANGYO KAISHA, Ltd. Substituierte Pyridinsulfonamide oder deren Salze, Verfahren zur Herstellung und diese enthaltende Herbizide
US5583231A (en) * 1991-01-24 1996-12-10 Ishihara Sangyo Kaisha, Ltd. Certain 2-alkanesulfonamido-pyridine derivatives
US5284945A (en) * 1991-04-11 1994-02-08 Hoechst Aktiengesellschaft Process for the preparation of 2-pyridylsulfonylureas
EP0508348A1 (de) * 1991-04-11 1992-10-14 Hoechst Schering AgrEvo GmbH Verfahren zur Herstellung von 2-Pyridylsulfonylharnstoffen und Thiadiazolopyridine als Zwischenprodukte in diesem Verfahren
US5235050A (en) * 1991-04-11 1993-08-10 Hoechst Aktiengesellschaft Thiadiazolopyridines
EP0521500A1 (de) * 1991-07-05 1993-01-07 Hoechst Schering AgrEvo GmbH Salze von Pyridylsulfonylharnstoffen als Herbizide und Pflanzenwachstumsregulatoren, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0555770A1 (de) * 1992-02-14 1993-08-18 Hoechst Schering AgrEvo GmbH N-Heteroaryl-N'-(pyrid-2-yl-sulfonyl)-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
US5847146A (en) * 1992-02-14 1998-12-08 Hoechst Schering Agrevo Gmbh N-heteroartyl-n'-(pyrid-2yl-sulfonyl) ureas, processes for their preparation, and their use as herbicides and plant growth regulators
US6316388B1 (en) 1992-02-14 2001-11-13 Hoechst Schering Agrevo Gmbh N-heteroaryl-N′-(pyrid-2-yl-sulfonyl) ureas, processes for their preparation, and their use as herbicides and plant growth regulators
EP0562731A1 (de) * 1992-03-10 1993-09-29 ISHIHARA SANGYO KAISHA, Ltd. Substituierte Pyridinsulfonamidverbindungen und ihre Salze, Verfahren zu ihrer Herstellung und diese enthaltende Herbizide
TR27073A (tr) * 1992-03-10 1994-10-12 Ishihara Sangyo Kaisha Ikame edilmis piridinsülfonamid bilesigi ya da tuzu bu bilesik ya da tuzunun hazirlanmasi icin islem ve bu bilesik ya da tuzunu ihtiva eden herbisid.
US5663118A (en) * 1992-06-08 1997-09-02 Hoechst Schering Agrevo Gmbh Fluoromethylsulfonyl-substituted pyridylsulfonylureas as herbicides, process for their preparation, and their use
FR2703685A1 (fr) * 1993-04-09 1994-10-14 Hoechst Schering Agrevo Gmbh Pyridylsulfonylurées à substitution fluorométhylsulfonyle, utilisées comme herbicides, procédé pour les prépararer, et leur utilisation.

Also Published As

Publication number Publication date
ES2089041T3 (es) 1996-10-01
JPH04234850A (ja) 1992-08-24
GR3020583T3 (en) 1996-10-31
GR3033519T3 (en) 2000-09-29
EP0451468B2 (de) 2000-03-08
DK0451468T3 (da) 1996-09-09
US5139565A (en) 1992-08-18
DE69119135T2 (de) 1996-10-31
DE69119135D1 (de) 1996-06-05
ES2089041T5 (es) 2000-07-16
ATE137500T1 (de) 1996-05-15
EP0451468B1 (de) 1996-05-01

Similar Documents

Publication Publication Date Title
EP0184385B1 (de) N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3-trifluoromethylpyridin-2-sulfonamide oder Salze davon, diese enthaltendes herbizides Mittel und Verfahren zur Herstellung dieser Verbindung
EP0388994B1 (de) Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zur Herstellung dieser Verbindungen
US4420325A (en) Herbicidal sulfonamides
US4191553A (en) Herbicidal sulfamates
JPH0774206B2 (ja) 複素環式２―アルコキシフエノキシスルホニル尿素類、それらの製造方法およびそれらを含有する除草剤
EP0451468B2 (de) Substituierte Pyridinsulfonamidverbindungen, diese enthaltende herbizide Zusammensetzungen und Verfahren zu ihrer Herstellung
US4661147A (en) Herbicidal sulfonamides
EP0161905B1 (de) Herbizide Halopyrimidine
JP2787590B2 (ja) 複素環置換フエノキシスルホニル尿素、それらの製造方法および除草剤または植物生長調整剤としての用途
US4778512A (en) Herbicidal heterocyclic sulfonamides
US4604131A (en) Herbicidal sulfonamides
EP0496608B1 (de) Substituierte Pyridinsulfonamide oder deren Salze, Verfahren zur Herstellung und diese enthaltende Herbizide
JP2997287B2 (ja) ３―置換アルキルサリチレートを基礎としたフエノキシスルホニル尿素、それらの製造方法およびそれらの除草剤および植物生長調整剤としての使用方法
US4835282A (en) Isothiazoles as intermediates for herbicidal sulfonamides
US4822402A (en) Thiophenesulfonamide compounds, and herbicidal compositions containing them
US4705556A (en) Herbicidal sulfonamides
US4878938A (en) Herbicidal Sulfonamides
US4906278A (en) Herbicidal heterocyclic sulfonamides
US4897108A (en) Herbicidal sulfonamides
US4935528A (en) Thiophenesulfonamide compounds, herbicidal compositions containing them, and process for their production
EP0562731A1 (de) Substituierte Pyridinsulfonamidverbindungen und ihre Salze, Verfahren zu ihrer Herstellung und diese enthaltende Herbizide
US5011527A (en) Herbicidal heterocyclic sulfonamides
US4764204A (en) Herbicidal sulfonamides
JP2567353B2 (ja) 置換ピリジン系化合物
JP2007246477A (ja) スルホニルウレア化合物および除草剤

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

17P Request for examination filed

Effective date: 19920310

17Q First examination report despatched

Effective date: 19940217

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

REF Corresponds to:

Ref document number: 137500

Country of ref document: AT

Date of ref document: 19960515

Kind code of ref document: T

ITF It: translation for a ep patent filed
REG Reference to a national code

Ref country code: CH

Ref legal event code: NV

Representative=s name: A. BRAUN, BRAUN, HERITIER, ESCHMANN AG PATENTANWAE

REF Corresponds to:

Ref document number: 69119135

Country of ref document: DE

Date of ref document: 19960605

ET Fr: translation filed
REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3020583

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2089041

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2089041

Country of ref document: ES

Kind code of ref document: T3

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

26 Opposition filed

Opponent name: HOECHST SCHERING AGREVO GMBH.

Effective date: 19970203

NLR1 Nl: opposition has been filed with the epo

Opponent name: HOECHST SCHERING AGREVO GMBH.

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

PUAH Patent maintained in amended form

Free format text: ORIGINAL CODE: 0009272

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: PATENT MAINTAINED AS AMENDED

27A Patent maintained in amended form

Effective date: 20000308

AK Designated contracting states

Kind code of ref document: B2

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

ITF It: translation for a ep patent filed
REG Reference to a national code

Ref country code: CH

Ref legal event code: AEN

Free format text: MAINTIEN DU BREVET DONT L'ETENDUE A ETE MODIFIEE

ET3 Fr: translation filed ** decision concerning opposition
NLR2 Nl: decision of opposition
NLR3 Nl: receipt of modified translations in the netherlands language after an opposition procedure
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: THE PATENT HAS BEEN ANNULLED BY A DECISION OF A NATIONAL AUTHORITY

Effective date: 20000526

REG Reference to a national code

Ref country code: ES

Ref legal event code: DC2A

Kind code of ref document: T5

Effective date: 20000608

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GR

Payment date: 20060111

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20060205

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20060207

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 20060213

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20060215

Year of fee payment: 16

Ref country code: GB

Payment date: 20060215

Year of fee payment: 16

Ref country code: DK

Payment date: 20060215

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20060220

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20060227

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20060228

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 20060303

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20060317

Year of fee payment: 16

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20060410

Year of fee payment: 16

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070221

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070228

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070228

REG Reference to a national code

Ref country code: DK

Ref legal event code: EBP

Ref country code: CH

Ref legal event code: PL

EUG Se: european patent has lapsed
GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20070220

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 20070901

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070220

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20071030

BERE Be: lapsed

Owner name: *ISHIHARA SANGYO KAISHA LTD

Effective date: 20070228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070901

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070901

Ref country code: DK

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070220

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070228

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20070221

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070221

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070220

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070220